Newman is very good on this issue. He points out how difficult real repentance is and how tempting to avoid it or replace it with something else. This is why apologies are often flawed.
…they come couched in equivocal language ("I'm sorry if you were offended by what I said"), which subtly shifts responsibility from what I said to how the other person heard it. Or we say the right words, but without the tone of genuine remorse in our voice that alone communicates sincerity.
A real apology represents and communicates an inner transformation of the wrongdoer. He both owns and disowns what he did. He owns it by admitting that he did it and that it was wrong. He disowns it by regretting it, by making amends, and by avoiding it in the future. A sincere apology, says Newman quoting Richard Cross, "obviously gives something to the wronged party." One of the things it gives is the space to forgive.
A false apology, by contrast, represents a desire to "move on" combined with an unwillingness to admit real fault or to commit to real change. It does not give, but rather demands something of the wronged party: namely, that he forget about the whole thing, pretends that it wasn't a big deal, etc. It wants the wronged party to give up his protest and essentially acquiesce in his own mistreatment. False apologies don't liberate but manipulate the offended party.
This brings me to a section of the book that seems to me incomplete and open to misinterpretation. Newman wants to stress that it is difficult to apologize. We may have to do it several times and even enlist our friends to attest to our sincerity. I agree with him on that point. But then he quotes the following passage from Maimonides, which strikes me as a bit off:
Even if one only injured the other in words [and not deeds], he must pacify him and approach him until he forgives him. If his fellow does not wish to forgive him, the other person brings a line of three of his friends who [in turn] approach the offended person and request from him [that he grant forgiveness]. If he is not accepting of them, he brings a second [cadre of friends] and then a third. If he still does not wish [to grant forgiveness], one leaves him and goes his own way, and the person who would not forgive is himself the sinner.
To me, the wrongdoer in this passage comes across as too demanding. He does not just hope for forgiveness but wants to force the issue. He thinks that since he has done his part by apologizing, he now has a right to be forgiven. And, if necessary, he is justified in calling upon the wider community to put more pressure on the recalcitrant injured party. This seems to me all wrong—a form of re-victimizing the victim. In cases like this the wrongdoer is better advised to do some more soul-searching because it is likely that his apology is not really sincere or appropriate. (The expectation of being forgiven diminishes as the awareness of the injury done increases.) Even if his apology is heartfelt and real, he has no right to force the issue. He owes the person he has injured the time and space needed to absorb the pain and recover from it.
(According to Newman, "Judaism teaches that the offenses we commit against others cannot be forgiven by God ... unless those we have harmed forgive us first." I don't know if this is true, but it would make a more aggressive approach to obtaining forgiveness understandable in the Jewish context. I don't think, however, that God's forgiveness of our sins is conditional like that upon the forgiveness of those we sinned against.)
The passage from Maimonides brings to mind the one in Matthew (18:15-17):
If your brother sins against you, go and tell him his fault between you and him alone. If he listens to you, you have won over your brother. If he does not listen, take one or two others along with you, so that ‘every fact may be established on the testimony of two or three witnesses.’ If he refuses to listen to them, tell the church. If he refuses to listen even to the church, then treat him as you would a Gentile or a tax collector.
The all important difference, of course, is that here Jesus is telling us how to deal with the wrongdoer, whereas Maimonides is giving instructions about how to approach the victim. The two cases are not symmetrical. Repentance is a strict requirement of justice. Forgiveness, though we are all called to it, remains essentially gratuitous.